Michele and Buster: A Tranny Tale

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and adultery. If any of these themes offend you, then I suggest you close the story now; but please don't complain; you have been warned!

In my previous true stories I have provided some insights into how I became a part-time transvestite and I have also expressed my views on my own particular type of transvestism; a sort of self-psychoanalysis if you will. I intend to discuss my own views on this subject further before I launch into the story, so if you're here for the sex, drugs and rock and roll you might want to skip the first few paragraphs.

I know that there are all sorts of transgender affectations and all sorts of sexual and psychological reasons why guys want to dress as women or actually switch genders. I want to describe my own affectations here because I think they are relevant to my story, to me, and particularly relevant to Buster (although far be it from to me to say that I know anything about Buster's life, other than what he told me.......and as Dr Gregory House wound say: "everybody lies!").

I know that there are all types of 'gender-benders' out there, from 'hairy-legged panty wearers' to gorgeous transsexuals whom you wouldn't have even known had once been men. I find it simple for me to use the following labels (The labels are for ME ok; before I get a thousand e-mails about how unfair it is to 'label' people).

The guys who are just panty-wearers or lingerie lovers or who like to dress in women's clothes but make no attempt to look feminine are obviously fetishes. Guys who sometimes wear full female attire, wigs and makeup, I call crossdressers (and I am constantly reminded that most of them are heterosexual (did I use another label?)). Those that go a step further and shave most or all of their body hair, effect female persona when dressed and can be classed as 'passable' (fuck, I just used yet another label) I call transvestites.

After that, for me, it gets difficult because there are transvestites who just like to dress occasionally and look passable as a woman, those who just like to dress occasionally and look passable as a woman and have lots of sex (like me), and those who dress full time and who are on their way to becoming transsexuals. And then of course there are the transsexuals themselves who live their lives as women and are usually on HRT and have, or will undertake, surgery to correct nature's mistakes.

There, now if I haven't pissed off most of the transgendered community I will be surprised; but as I said these labels work for ME.

I tell you about this because during my life I have developed from a fetish to a transvestite. As long as I can remember I have had a fetish for nylons. Stockings, pantyhose or tights on a good pair of legs still turn me on whether I am in male or female mode and whether a genetic female or a transgender wears them. My earliest sexual memories are of touching nylon clad legs (and yes they were often mom's, aunties, cousins etc but I'm not going down that route - read some of my non-transgendered fiction if that subject turns you on) and when I reached adolescence and first discovered the joys of masturbation one of the first things I did was steal a stocking and enjoy the sensual feel of nylon on my manhood.

Whenever I could, I would get my girlfriends to leave their nylons on during sex and most of them soon figured out my fetish even if I didn't tell them about it. Women whom I felt I could really trust, I would ask if they minded me also wearing pantyhose during sex. Of course it hadn't taken me long to try wearing hosiery, probably the day after my first wank, and I often wore nylons during solo sex. I also started to wear nylon and satin panties and sometimes slips, just to increase the lovely sensuous feel of nylon, satin and Lycra or other sexy materials against my body.

I eventually married and am fortunate that my wife is tolerant of my nylon fetish and has come to enjoy it herself. Over the years we have had many wonderful sexual encounters with both of us wearing sheer pantyhose and sometimes with her wearing stockings. Of course I never told her that I wear nylons and lingerie during masturbation.

I travelled overseas extensively and I admit to being promiscuous and trying all types of sexual peccadillos and as I tried all of the forms of sexual experimentation I became increasingly fascinated with transvestites. I have never considered myself gay or bisexual; I consider myself 'sexual'. There aren't many sexual perversions (a label?) that I haven't tried (paedophilia, scat and necrophilia are probably where I draw the line) but I have always been fascinated by sexy transvestites.

Then there was this huge explosion in the world of sex. The Internet! There is probably more sex happening in cyber-space than in suburban bedrooms. Being a nylon fetish I was in heaven; there were all sorts of websites with pictures and stories of women in pantyhose or stockings. Women were having sex all over the web whilst dressed in sexy lingerie and nylons. I also found that I could enter chat rooms and talk to like-minded men and women (think some of those women might have been men pretending to be women?......nah......they had pictures in their profiles for god sake!) and I even got caught up in the web-cam craze.

I spent many a lazy afternoon masturbating in front of my PC wearing nylons whilst looking at pictures of women and sometimes men wearing nylons; I also 'cammed' with men who had similar fetishes. Face shots were of course a no-no! My search engine often led me to transvestite sites and chat rooms and I got even more pleasure from the net. It was about this time that I went further and purchased my first women's clothes. Sure I had bought lingerie and hosiery before, but I bought a skirt, blouse and high heels and began to dress up as a woman whilst chatting and camming. I was shaving my legs and hands and painting my nails now, but as I never showed my face, I could have all sorts of fun on the net.

My fascination with crossdressing grew and I eventually bought a wig and makeup and began to fully crossdress. I won't bother tell the story about my progress from clumsy crossdresser to refined (in my opinion anyway) part-time transvestite as you can read all about in the previous "True Story" instalments.

What I'm emphasising here is that I have developed from a nylon fetish (a fetish which I still have of course) to a "fully blown" (pardon the pun) transvestite. That is where I intend my transformation to stay. I have no wish to be a woman or even a full-time transvestite. When I am not dressed as a woman I sometimes daydream and 'become' Michele in my head, but I have no feminie feelings except when I am dressed as a woman; and then those feelings are sexual. When I'm dressed I like to be treated as a woman and behave like a woman for sexual gratification; that's all there is to it.

The purist 'transgender police' will argue that there is more to it than that, and that I have a latent desire to become a woman. Well to them I say bollocks! I don't want to be a woman; I want to be a transvestite; god, I love to dress in sexy women's clothes and makeup and have sex! Sex, sex, sex, sex! That's what it's about for me, whether it's with a woman, man, a TV or CD.

So............on with this true story.

I advertise myself on a number of websites and I received a message from an admirer named Buster on my tvchix website (if you log in you can see my profile and Buster's there). His name was Buster and he was in a large city in Australia but travelled regularly and was a frequent visitor to the city where I had my bachelor pad. His profile on tvchix reads as follows:

"Profile: Admirer Favourite Look: Classy / Stylish

Hi, Just your average admirer. Used to dress a few years ago but just stopped looking good. The fortunate thing is I do really understand the reasons why we do dress up.

Buster is also interested in: Boots, Can Travel, Trendy/Modern club wear, Experienced"

So this guy looked just the type I might be interested in. You will note that Buster 'used to dress'; and that will become important as the story unfolds.

We emailed back and forth and he said he liked the way I looked and also that he was a huge leg man and nylon fetish. Mmmmm a nylon fetish that used to crossdress; did that ring any bells with me? All I had to do was look in the mirror! (The difference being of course is that I still dress.)

We finally arranged a meeting at my place one evening and I was very excited. When Buster arrived in town that afternoon he called me on my cell-phone and I gave him my address. Ever the gentleman, he asked me what I liked to drink and said he would stop on the way over and get some drinks. As we had conversed by email I had an idea of his tastes but I asked him what he would like me to wear for the meeting. He said he would like me to wear what I was wearing in my profile pic on Tvchix and also requested I wear pantyhose as well as stockings.

As he had some business to finish, I had plenty of time to get myself prepared for the meeting. I painted my toenails with my favourite plum-red nailpolish. Doing my toenails is so much easier than doing my fingernails so it didn't take long to get two coats on and let them dry while I went to my wardrobe and took out the clothes I was going to wear and lay them on the bed.

I took care of my hygiene (funny how no one mentions that unsavoury part of being a transvestite, anal hygiene) and then showered and shaved. I poured myself a glass of red wine and commenced my transformation. I love getting dressed up as Michele and I often describe it in my stories and I intend to do so again. The anticipation and sensuality of changing from a naked man to a sexy transvestite is a lovely experience.

I stood at my vanity mirror in the bathroom determined to do really good job on my makeup. I applied a liberal amount of foundation and then coated my face and neck with finishing powder; the powder one shade darker than my foundation. I always do my eyeliner next. All of the makeup tips in books, magazines and online say you should do this later but I find, for me anyway, that this is the hardest part of applying my makeup and if I mess it up I can simply wipe it off, apply more foundation and start again without ruining my eye-shadow and mascara. I applied the eyeliner liberally to my upper and lower eyelids, from the inner corner of my eyes to the outer corners, gradually thickening the line.

I opened my eyeshadow and selected pale blue which I applied to my eyelids and then blended a shade of dark pink onto the upper part of my eye sockets and right up to my eyebrows. Next I rouged my cheeks to define the lines of my cheekbones. I always use more rouge and eye shadow than is the fashion nowadays but I like the 'heavy makeup' look and style of the eighties over the current subdued 'less is more' look.

I carefully brushed lashings of mascara onto my lower and upper eyelashes. I like to wear lots of mascara, and I managed to get my lashes thoroughly coated without clotting it. I took my time to apply the 'Lasting Colour' lipstick to my lips. I applied it carefully just outside of my lip-line so that my lips would seem fuller; the 'Raging Ruby' lipstick set off my plum red nail polish nicely. I finished with another coat of face powder and retired to my bedroom to dress.

At this stage of my transformation I often giggle to myself; I look kind of weird I suppose; a naked man with a fully made-up face and short hair prancing around his flat. That said I do get excited by the taste and feel of the cosmetics.

I sat down on my bed and stepped into a pair of taupe sheer to the waist pantyhose and smoothed them up my legs and around my buttocks. If I am wearing pantyhose as a foundation garment and intend to wear stockings over them I usually use a cheap generic brand. Because Buster had indicated his nylons fetish to me and specifically requested I wear both pantyhose and stockings for his pleasure; this time I wore Kolotex Voodoo, an expensive Australian brand of ultra-sheer fashion pantyhose.

I stood up and stepped into a black lace and lycra suspender belt and then unwrapped a pair of Kayser 15 denier sheer 'grey-mist' stockings, which I slid, up my legs over the taupe pantyhose and clipped them to the garters hanging from my suspender belt. My legs looked very sexy under the two layers of sheer nylon and my painted toes peeped through the gossamer hosiery.

I stepped into a pair of sheer mauve full-cut panties with small white flowers embroidered on them and pulled them up my legs, taking care not to snag them on the clips of my garters; I smoothed them around my buttocks and tucked my penis under the gusset. I pulled on my black lace and lycra brasserie and stuffed my homemade breastforms into the cups. I adjusted the bra so that it sat properly on my frame and then prepared to finish dressing. I had poured myself a glass of red wine which I had drained and I took the time to go downstairs and refill my glass. I checked the blinds were closed and glanced at the clock; plenty of time!

I went back upstairs to my bedroom and steeped into my navy blue skirt and pulled it up, zipped up the side and adjusted it at the waist so that it sat properly. The hem came to about six inches above my knees and it had nice little split at the back that showed off more of my legs. I pulled the satin lining from my legs where it had clung to my nylon stockings. I slid into my mauve satin long-sleeved blouse and buttoned it up and finished off the outfit with black patent-leather high-heeled sandals with ankle straps. I opened the wardrobe and took out the wig from its makeshift wigstand and brushed it out. My favourite wig is a dark brunette with scarlet highlights. I adjusted the brunette bob so that the fringe just covered my eyebrows and the hair was evenly distributed around my shoulders. I went back to the bathroom and applied another coat of lipstick and a final dusting of face powder.

I collected my nailpolish, jewellery, perfume and my glass of wine and headed downstairs to the lounge. I turned off the overhead lights and turned on the table-lamp and dimmed it so that the room had nice cosy glow. I refilled my glass and lit a cigarette and set about the difficult task of putting on my bangles and bracelets. The bangles slipped on easily enough but I had to lay my wrists flat on the table to close the snap-clips on my bracelets. After much swearing and whinging I managed to complete the task.

I bent down and clipped a gold anklet around my left ankle and then stood in front of the wall-mirror and clipped a string of 'choker-chain' pearls around my neck followed by a ruby pendant necklace. I clipped matching ruby earrings to my ears and flicked my hair back into place. I sprayed my favourite Poison perfume liberally on my décolletage and also gave a quick spray under my skirt. I sat back down and painstakingly painted my fingernails with the plum coloured nailpolish. I let it dry while I sipped my wine and watched an x-rated DVD which I had qued up earlier.

I was ready for the meet and glanced anxiously at my mobile phone where it sat on the coffee table. I was now very anxious; would I meet Buster's expectations?

Would he look as good as the picture he had emailed to me? (not that I am concerned with looks really). I gulped my wine and lit another cigarette. My cell-phone vibrated and buzzed; the window on the phone displayed "incoming call", "Buster."

I snatched it up and answered the call.

"Hi Michele, I'm in a taxi and have just left the bottle-shop and have the drinks. I'll be about five minutes is that ok?" he asked.

"Perfect," I answered.

"See you soon sexy," he relied and wrung off.

I felt sexy and feminine; he was so polite and obviously as anxious to meet as I was.

A few minutes later the headlights of a car flashed across my lounge room blinds; it could only be one person. I stood up and smoothed and straightened my skirt and went over to window and peeked out. A man had alighted from the taxi and was making his away along the path to my door. I unlocked the door and opened it an inch and stood back, posing to make a good first impression on Buster.

Buster came through the door, carrying a large package. He smiled at me and went over to the table to put down the package as I closed and locked the door behind him. He looked me up and down and I felt myself becoming aroused as he brazenly examined my face, body and legs.

"Well?" I asked.

He strode over to where I stood and looked into my eyes.

"Perfect," he said and he took me into his arms and kissed me deeply.

Our lips crushed and his tongue explored my mouth. I felt him stiffen in his pants and he pulled me hard against him so that I could feel his erection against my body. He wasted no time as his hand slid down to my buttocks, squeezing them and caressing them through my skirt before sliding up under my skirt and stroking my thighs. Buster's fingers explored my stocking tops and then followed my garter straps up to my panties.

"You remembered," he smiled, "Stockings over pantyhose; you naughty girl."

I smiled back and led him to the lounge where we sat down and smooched for a minute or two.

"Let's get us a drink," Buster said and took the package over to the kitchen counter.

He took out cans of UDL vodka and tonic and poured us both large drinks over ice. He put the rest of the drinks in the fridge and then went back to the package where he rummaged around and produced another parcel. The parcel was inside a bag bearing the logo of David Jones; a quality department store.

"Presents for later," he smiled and came back to the lounge and sat down next to me.

We both sipped our drinks and Buster lit cigarettes for both of us.

"So what do you like?" he asked stroking his hand along my nylon-encased thighs.

"Well I like that," I giggled.

"I like anything really, top, bottom or whatever. I prefer to bottom though and I like to keep most of my clothes on during sex." I went on, "it makes me feel feminine if I'm dressed."

"A girl after my own heart," he smiled, "Do you like role play? Bondage? Watersports?" he asked.

"Sure; I love role play and am willing to try watersports if we can do it the bathroom," I answered.

Buster kissed me again and pushed me down into the sofa and climbed on top of me. His hands were everywhere under my skirt stroking my thighs and buttocks. He freed my stiffening member from my panty crotch and stroked it though the panty material. I gasped and reciprocated, stroking his thickening member through his jeans.

I extricated myself from under him whilst still kissing and fondling him.

"Let me see it," I gasped and dropped to my knees between his legs.

He leaned back on the couch and looked down at me smiling.

"You are a dirty girl, aren't you," he grinned.

My painted nails raked his thickening member through his trousers and then I undid his fly and freed his engorged phallus. Buster's cock is not exceptionally long but it is very thick and I reached out and stroked the smooth skin of his shaft and slid my fingers over his glans, coating it with the dewy drop of pre-seminal fluid that had formed on the eye. Buster gasped and leaned forward gently easing my head down into his lap.